The most likely policy shift is one that restricts travel more (right now travel authorizations are quite broad) but not entirely, and to try and maintain benefits for Cuban entrepreneurs instead of the state (i.e. the military). The tricky thing is that the two are partially contradictory. For example, you want more Americans going to Cuba and using Airbnb, because that money is going into people's pockets.

Assuming the administration really does make its announcement tomorrow, your best guess is that the talk will be tough, the Cuban government will be referred to as "very, very bad" and Obama will be labeled as "appeaser," then the actual details will be mostly continuity.

The Cuban American National Foundation hasn’t sent the administration a letter or position paper, partly because with so many unfilled positions in the Trump administration and uncertainty over who is really driving Cuban policy, “the question is who do you talk to?” said José “Pepe” Hernández, president and one of the founders of the exile organization. “It’s very confusing, really.”